Paint and body

[SPoe]

My 93 is once again rusting on the roof of the cab and I just want to paint the whole truck the newer Ram khaki color but the guy told me that all the plastic molding on the sides would be difficult to get back on, if possible. So i have two questions.

1. What is the best method that y'all have found in taking off the plastic molding

and

2. What is the best method in filling in the holes around tires because there are two holes on each side

Ive never done any body work so this is all new to me